EP0054668B1 - Procédé de préparation de iodo-organyl-alkoxysilanes - Google Patents

Procédé de préparation de iodo-organyl-alkoxysilanes Download PDF

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Publication number
EP0054668B1
EP0054668B1 EP81108621A EP81108621A EP0054668B1 EP 0054668 B1 EP0054668 B1 EP 0054668B1 EP 81108621 A EP81108621 A EP 81108621A EP 81108621 A EP81108621 A EP 81108621A EP 0054668 B1 EP0054668 B1 EP 0054668B1
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EP
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Prior art keywords
group
carbon atoms
mol
iodide
process according
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EP81108621A
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German (de)
English (en)
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EP0054668A3 (en
EP0054668A2 (fr
Inventor
Peter Dr. Panster
Alfons Dr. Karl
Wolfgang Dr. Buder
Peter Dr. Kleinschmit
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Evonik Operations GmbH
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Degussa GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1888—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of other Si-linkages, e.g. Si-N

Definitions

  • the invention relates to a process for the preparation of (iodorganyl) alkoxisilanes, which allows the preparation of this class of compounds in a considerably shorter reaction time and a significantly higher yield than in the prior art.
  • Halogenorganyl alkoxisilanes are valuable chemical reagents. They are used e.g. for the modification of inorganic support materials having reactive surface groups, in particular OH groups, for the synthesis of functional (organyl) alkoxisilyl-substituted compounds, including corresponding ammonium compounds, which are used as surfactants, algicides or bactericides or they generally constitute intermediates in the preparation other important silanes.
  • Examples of each of these areas of application include. a. described in European patent application 0 008 902, in DE-AS 10 23 462, US-PS 4 093 642, DE-OS 22 22 997, DE-OS 24 08 192 and in DE-AS 21 41 159 .
  • alkoxysilanes would be the most suitable from the point of view of reactivity (iodine organyl), only the chlorine or bromine organyl derivatives have been used to date. The reason for this can be seen in the fact that these halogen compounds have hitherto been considerably easier and accessible in higher yield than the iodine homologs which are usually obtained by halogen exchange; this describes e.g. M.G. Voronkov et al. in Zhurnal Obshchei Khimii 45, 9, 2010 (1975).
  • R 1 represents a straight-chain or branched alkylene group having 1 to 20 C atoms, a cycloalkylene group having 5 to 8 C atoms and units of the following type, respectively.
  • n indicates the number of the halogen-containing methylene group between 1 and 6 and m can be a number from 0 to 6
  • R 2 stands for an alkoxy grouping with 1 to 5 carbon atoms, the methoxy thoxy or the ethoxy thoxy group
  • R 3 and R 4 - can have the same meaning as R 2 or for branched or linear alkyl groups containing 1 to 10 C atoms or for a phenyl group optionally substituted with a halogen atom and can be identical or different from one another, allowed in very short reaction times and high yields and can be practiced with significantly less effort compared to the previous procedure.
  • Aliquat 336 tricapryl (methyl) ammonium chloride
  • Aliquat 336 tricapryl (methyl) ammonium chloride
  • benzyltrimethylammonium chloride or hydroxide benzyltributylammonium chloride, tetra-n-butylammonium chloride, bromide, iodide or hydroxide, cetyltrimethylammonium chloride or bromide, tetra-n-pentylammoniumchlorid, tetra-n-hexylammoniumchlorid or bromide, tetrabutylammonium hydrogen sulfate, benzyltributylammonium chloride, Trimethyloctadecylammoniumbromid, tributylhexadecylphosphonium bromide, ethyltriphenylphosphonium bromide, tetraphenylphosphonium bromid
  • Suitable liquids which could also be called solvents or diluents, are cyclic or open-chain ethers, preferably tetrahydrofuran, dioxane, trioxane, diethyl, dipropyl and dibutyl ether, ethylene glycol dimethyl ether or chlorinated hydrocarbons, preferably methylene chloride, chloroform, 1,2-dichloroethane, 1,1,1-trichloroethane, trichlorethylene, chlorobenzene or aliphatic and aromatic nitro compounds, preferably nitromethane, nitroethane and nitrobenzene or aliphatic nitriles, preferably acetonitrile or propionitrile or else dimethylformamide, dimethyl sulfoxide, acetone, diethyl ketone or methyl ethyl ketone, and especially lower alcohol such as methanol , Ethanol, n- and i-propanol, n-
  • Typical silanes which can be prepared by the process according to the invention are, for example, J- (CH 2 ) 3 --Si (OC 2 H 5 ) 3 , J- (CH 2 ) 3 -Si (OCH 3 ) 3 , J- (CH 2 ) 2 -Si- (OC 2 H 5 ) 3 , J-CH 2 -Si (OC 2 H 5 ) 3 , J-CH 2 Si- (OCH 3 ) 3 , J- (CH 2 ) 2 -Si ( OC 2 H 5 ) 3 , J-CH 2 -Si (OC 2 H 5 ) 3 , J-CH 2 -Si (OCH 3 ) 3 , J- (CH 2 ) 3 -Si (OC 2 H E ) 2 ( CH 3 ), J - (CH 2 ) 3 -Si (OC 2 H 5 ) - (C 6 H 5 ) 2 etc.
  • a favorable variant of the invention provides that the compounds of the formula (1) are prepared using NaI or KI in the alcohol corresponding to the alkoxy, methoxy thoxy or ethoxy thoxy group in each case silicon.
  • radicals R 2 , R 3 and R 4 have the same meaning.
  • anhydrous NaJ or KJ is preferably used as the iodide donor
  • other alkali metal iodides or also alkaline earth metal and ammonium iodides such as LiJ, MgJ 2 , CaJ 2 , SrJ 2 or BaJ 2 , NH 4 J, (H 3 C) 4 NJ can be used.
  • a quantitative conversion can be achieved with a stoichiometric molar ratio of iodide donor: (chloro-organyl) alkoxisilane. In the sense of a shorter total conversion time, however, a molar ratio between 1: 1 and 2: 1 is preferred.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)

Claims (4)

1. Procédé pour la fabrication de (iodorganyl)--alcoxysilanes répondant à la formule générale (1
Figure imgb0016
où R1 représente un groupe alcoylène linéaire ou ramifié à 1 à 20 atomes de carbone, un groupe cyclo- alcoylène'avec 5 à 8 atomes de C et des ensembles du type suivant:
Figure imgb0017
ou
Figure imgb0018
dans lesquelles n indique le nombre compris entre 1 et 6 des groupes méthylène fixés sur l'halogène et m peut être un nombre de 0 à 6, R2 représente un groupe alcoxy avec 1 à 5 atomes de C, qui peut être un groupe méthoxyéthoxy ou un groupe éthoxyéthoxy, R3 et R4 peuvent avoir la même signification que R2, où peuvent représenter des groupes alcoyle, ramifiés ou linéaires, contenant de 1 à 10 atomes de C, ou un groupe phényle éventuellement substitué par un atome d'halogène, et peuvent être semblables ou différents, par échange d'halogènes, procédé caractérisé en ce que l'on fait réagir les composés chlorés ou bromés correspondants avec des proportions stoechiométriques ou plus grandes, que l'on peut augmenter jusqu'au double de la proportion molaire, d'iodures de métaux alcalins, alcalino-terreux ou d'ammonium, en présence de 0,01 à 5 mol% d'un sel quaternaire d'ammonium, phosphonium, arsonium, stibonium, ou d'un sel tertiaire de sulfonium avec des substituants alcoyle, aryle ou aralcoyle, et un anion organique ou minéral ou encore un éther-couronne dans des éthers cycliques ou à chaîne ouverte, des hydrocarbures chlorés, ou des composés nitrés aliphatiques ou aromatiques, ou encore de la diméthylformamide, ou diméthylsulfoxyde, de l'acétone, diéthylcétone ou méthyléthylcétone, et en particulier des alcools inférieurs.
2. Procédé suivant la revendication 1, caractérisé en ce que la réaction peut être réalisée dans les tétra- hydrofuranne, dioxane, trioxane, éthers diéthylique, dipropylique et dibutylique, diméthyléther d'éthy- lèneglycol, ou hydrocarbures chlorés, de préférence les chlorure de méthylène, chloroforme, 1,2-di- chloréthane, 1,1,1-trichloréthane, trichloréthylène, chlorobenzène, ou des composés nitrés aliphatiques et aromatiques, de préférence les nitrométhane, nitroéthane et nitrobenzène, ou des nitriles aliphatiques, de préférence les acétonitrile ou propionitrile, ou aussi les diméthylformamide, diméthylsulfoxyde, acétone, diéthylcétone ou méthyléthylcétone et en particulier les alcools inférieurs tels que les méthanol, éthanol, n- et i-propanol, n- et i-butanol, ainsi que le pentanol.
3. Procédé suivant l'une des revendications 1 et 2, caractérisé en ce que les composés de formule (1) sont fabriqués en utilisant de l'iodure de sodium ou de potassium dans l'alcool correspondant aux groupes alcoxy, méthoxy, ou éthoxyéthoxy, fixés chaque fois sur le silicium.
4. Procédé suivant l'une quelconque des revendications 1 à 3, caractérisé en ce que R2, R3 et R4 ont la même signification.
EP81108621A 1980-12-19 1981-10-21 Procédé de préparation de iodo-organyl-alkoxysilanes Expired EP0054668B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3047995 1980-12-19
DE3047995A DE3047995C2 (de) 1980-12-19 1980-12-19 Verfahren zur Herstellung von (Jodorganyl)-alkoxysilanen

Publications (3)

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EP0054668A2 EP0054668A2 (fr) 1982-06-30
EP0054668A3 EP0054668A3 (en) 1982-10-13
EP0054668B1 true EP0054668B1 (fr) 1985-01-16

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US (1) US4362885A (fr)
EP (1) EP0054668B1 (fr)
JP (1) JPS57128694A (fr)
DE (2) DE3047995C2 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3800564C1 (fr) * 1988-01-12 1989-03-16 Degussa Ag, 6000 Frankfurt, De
DE4130643A1 (de) * 1991-09-14 1993-03-18 Degussa Verfahren zur reinigung von alkoxysilanen
DE4142129C1 (fr) * 1991-12-20 1993-07-01 Degussa Ag, 6000 Frankfurt, De
DE4223539C1 (de) * 1992-07-17 1993-11-25 Degussa Geformte Sulfonatgruppen-haltige Organopolysiloxane, Verfahren zu ihrer Herstellung und Verwendung
US5466767A (en) * 1992-08-06 1995-11-14 Degussa Aktiengesellschaft Shaped organosiloxane polycondensates, process for their preparation and use
DE4409140A1 (de) * 1994-03-17 1995-09-21 Degussa Wäßrige Lösungen von Organopolysiloxan-Ammoniumverbindungen, ihre Herstellung und Verwendung
WO2005077321A1 (fr) * 2004-02-13 2005-08-25 Kettenbach Gmbh & Co. Kg Produit dentaire a base de polyethers a fonction alcoxysilyle
DE102005031201A1 (de) * 2005-07-01 2007-01-25 Kettenbach Gmbh & Co. Kg Zu formstabilen Formkörpern aushärtendes kondensationsvernetzendes Dentalmaterial
KR100673554B1 (ko) * 2005-10-24 2007-01-24 한국과학기술연구원 트리플루오로메틸트리알킬실란의 제조방법
CN107864649B (zh) * 2016-05-19 2021-07-20 乔治洛德方法研究和开发液化空气有限公司 经由卤化物交换反应制备含Si-H碘代硅烷
US10384944B2 (en) 2016-05-19 2019-08-20 L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude Preparation of Si—H containing iodosilanes via halide exchange reaction

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US3125594A (en) * 1964-03-17 Process for the preparation of halo-
US2803638A (en) * 1954-08-18 1957-08-20 Gen Electric Method for preparing chlorophenylchlorosilanes
US2972638A (en) * 1958-09-02 1961-02-21 Minnesota Mining & Mfg Process for making fluorinated compounds
US3342898A (en) * 1963-05-13 1967-09-19 Diamond Alkali Co Composition and process
DE1242615B (de) * 1965-11-20 1967-06-22 Bayer Ag Verfahren zur Herstellung von Methyl-(brommethyl)-chlorsilanen
US3390976A (en) * 1966-05-11 1968-07-02 Dow Chemical Co Method for modifying the growth characteristics of plants
US3780127A (en) * 1972-10-02 1973-12-18 Union Carbide Corp Catalytic process for dehydration of alcohols
JPS5212703B2 (fr) * 1972-10-30 1977-04-08
SU523100A1 (ru) * 1974-03-25 1976-07-30 Иркутский институт органической химии СО АН СССР "Способ получени (бромметил)или (иодметил)-трихлорсиланов
SU503881A1 (ru) * 1974-06-11 1976-02-25 Иркутский институт органической химии Способ получени /иодалкил/тригалогенсиланов

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Angewandte Chemie, Band 86 (S), Seite 194, 1974 *
Phase Transfer Catalysis Principles and Techniques, C.M. Starks and C. Liotta, Seiten 60,61,77, 112-125 *

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Publication number Publication date
JPS57128694A (en) 1982-08-10
DE3047995C2 (de) 1984-05-10
US4362885A (en) 1982-12-07
EP0054668A3 (en) 1982-10-13
EP0054668A2 (fr) 1982-06-30
DE3047995A1 (de) 1982-07-08
DE3168379D1 (en) 1985-02-28

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